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[ CAS No. 1892-54-2 ] {[proInfo.proName]}

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Chemical Structure| 1892-54-2
Chemical Structure| 1892-54-2
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Product Details of [ 1892-54-2 ]

CAS No. :1892-54-2 MDL No. :MFCD00019108
Formula : C14H11N Boiling Point : No data available
Linear Structure Formula :- InChI Key :HUWRJSZODLRHMY-UHFFFAOYSA-N
M.W : 193.24 Pubchem ID :74691
Synonyms :

Safety of [ 1892-54-2 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1892-54-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1892-54-2 ]

[ 1892-54-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 75-21-8 ]
  • [ 1892-54-2 ]
  • [ 856377-58-7 ]
  • 2
  • [ 75-44-5 ]
  • [ 1892-54-2 ]
  • [3]phenanthryl isocyanate [ No CAS ]
  • 3
  • [ 85-44-9 ]
  • [ 1892-54-2 ]
  • 2-amino-benzo[<i>a</i>]naphthacene-8,13-dione [ No CAS ]
  • 4
  • [ 44830-55-9 ]
  • [ 1892-54-2 ]
  • 1-isopropyl-5-[3]phenanthryl-biguanide [ No CAS ]
  • 6
  • [ 1892-54-2 ]
  • [ 715-51-5 ]
YieldReaction ConditionsOperation in experiment
50% With tert.-butylnitrite; copper dichloride; In acetonitrile; at 0℃; for 1.33333h; General procedure: 3-amino-phenanthrene of 30g (155 mmol), of 36.7g CuBr2 (15 5 mmol) is dissolved in anhydrous acetonitrile 300 ml. Of 40.4ml tert- Butyl nitrile (535 mmol) is added in portions at 0C . The suspension was stirred for an additional hour, then poured into ice-water 400 ml, and stirred for about 20 minutes. The precipitated solid is filtered off with suction, dissolved in dichloromethane, washed several times with water. The organic phase was evaporated in a rotary evaporator is recrystallized from toluene / heptane. A yield of 21.9g (85 mmol) (55% of theory).
Step 3: 3-chlorophenanthreneCuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes then cooled down to 65 0C followed by the addition of 250 mL of dry acetonitrile and 26 g of t-butyl nitrite. The 3- phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3- chlorophenanthrene as a white solid.
With tert.-butylnitrite; copper dichloride; In acetonitrile; at 65℃; for 1.25h; Step 3; 3-chlorophenanthrene; CuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes then cooled down to 65 0C followed by the addition of 250 mL of dry acetonitrile and 26 g of ^-butyl nitrite. The 3- phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3- chlorophenanthrene as a white solid.
Step 3 : 3-chlorophenanthreneCuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes and then cooled to 65 0C. Dry acetonitrile (250 mL) and ?-butyl nitrite (26 g) were then added, followed by the addition of a solution of 3-phenanthrylamine (25 g) from Step 2 above, in acetonitrile (100 mL) over 30 minutes. The reaction was stirred for 45 minutes at 65 0C, then cooled to room temperature. To the reaction mixture was then added HCl (IN, IL). The aqueous layer was extracted with methylene chloride and the combined organic layers were washed successively with water and brine, dried over Na2SC4 and filtered. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica (100% hexanes) to afford a white solid which was recrystallized from hexane to yield 3- chlorophenanthrene (14.4 g) as a white solid.
With tert.-butylnitrite; copper dichloride; In acetonitrile; at 65℃; for 1.25h; CuCl2 (21 g) was dried under high vacuum at 115 C for 90 minutes then cooled down to 65 C followed by the addition of 250 mL of dry acetonitrile and 26 g of t-butyl nitrite. The 3-phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3-chlorophenanthrene as a white solid.

  • 7
  • [ 1892-54-2 ]
  • [ 715-50-4 ]
YieldReaction ConditionsOperation in experiment
55% With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0℃; for 1.33333h; 3-amino-phenanthrene of 30g (155 mmol), of 36.7g CuBr2 (15 5 mmol) is dissolved in anhydrous acetonitrile 300 ml. Of 40.4ml tert- Butyl nitrile (535 mmol) is added in portions at 0C . The suspension was stirred for an additional hour, then poured into ice-water 400 ml, and stirred for about 20 minutes. The precipitated solid is filtered off with suction, dissolved in dichloromethane, washed several times with water. The organic phase was evaporated in a rotary evaporator is recrystallized from toluene / heptane. A yield of 21.9g (85 mmol) (55% of theory).
32.9% With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 5℃; for 1.75h;Inert atmosphere; 82.0 g (423 mmol) of phenanthren-3-ylamine (XV) and 95.0 g (425 mmol) of copper(II) bromide are suspended in 1.70 l of acetonitrile and cooled to 0 C. 100 ml (1.33 mol) of tert-butyl nitrite are added dropwise over the course of 45 min at such a rate that an internal temperature of 5 C. was not exceeded, and the mixture is stirred at 0 C. for a further 1 h. The batch is added to 1.50 kg of ice, stirred for a further 30 min, the dark-brown solid is filtered off with suction and discarded. 1000 ml of ethyl acetate are added to the mother liquor, the organic phase is separated off, washed twice with 500 ml of 2 N HCl each time and twice with 500 ml of water each time, dried using sodium sulfate and subsequently evaporated to dryness. The residue is filtered through silica gel with a heptane/ethyl acetate mixture (10:1), corresponding fractions are evaporated and finally dried under reduced pressure. The yield is 35.9 g (140 mmol), corresponding to 32.9% of theory.
  • 8
  • [ 1892-54-2 ]
  • [ 605-87-8 ]
  • 9
  • [ 1892-54-2 ]
  • [3]phenanthryl-phenyl-diazene [ No CAS ]
  • 11
  • [ 106782-35-8 ]
  • [ 1892-54-2 ]
  • 12
  • [ 4120-78-9 ]
  • [ 1892-54-2 ]
YieldReaction ConditionsOperation in experiment
Step 2: 3-phenanthrylamineTo 385 g of polyphosphoric acic at 100 0C was added 32 g (0.14 mol) of l-(3- phenanthryl)ethanone oxime from Step 1 over 30 minutes. The mixture was stirred at 100 0C for 2 hrs, cooled down to room temperature followed by the addition of water/ice. Stirred 30 minutes, filtered and washed with water. This white solid was then placed in 500 mL of methanol and 40 mL of concentrated HCl. The reaction was refluxed overnight, cooled down to room temperature and concentrated down. A mixture of ethyl acetate/water was added to the residue and the resulting solution was made basic with 10 N KOH. The aqueous layer was extracted with ethyl acetate and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure to afford 25 g of 3-phenanthrylamine as a beige solid.
  • 13
  • [ 1892-54-2 ]
  • [ 108-24-7 ]
  • [ 4120-78-9 ]
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